US3770754A - Certai 1,2,4-oxa- and -thiadiazol-5-ylthioalkanoic acid derivatives - Google Patents
Certai 1,2,4-oxa- and -thiadiazol-5-ylthioalkanoic acid derivatives Download PDFInfo
- Publication number
- US3770754A US3770754A US00080165A US3770754DA US3770754A US 3770754 A US3770754 A US 3770754A US 00080165 A US00080165 A US 00080165A US 3770754D A US3770754D A US 3770754DA US 3770754 A US3770754 A US 3770754A
- Authority
- US
- United States
- Prior art keywords
- phenyl
- parts
- thiadiazol
- ylthio
- formula
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 239000002253 acid Substances 0.000 title description 9
- 230000008635 plant growth Effects 0.000 abstract description 8
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract description 5
- 239000005864 Sulphur Chemical group 0.000 abstract description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract description 5
- 239000005645 nematicide Substances 0.000 abstract description 5
- 229910052760 oxygen Inorganic materials 0.000 abstract description 5
- 239000001301 oxygen Substances 0.000 abstract description 5
- 150000001875 compounds Chemical class 0.000 description 33
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 30
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical class C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 19
- 125000000217 alkyl group Chemical group 0.000 description 16
- -1 carboxy, hydroxy Chemical group 0.000 description 16
- 239000000203 mixture Substances 0.000 description 15
- 239000002689 soil Substances 0.000 description 12
- 241000196324 Embryophyta Species 0.000 description 11
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 230000012010 growth Effects 0.000 description 9
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 125000004432 carbon atom Chemical group C* 0.000 description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 7
- 239000000080 wetting agent Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 125000003545 alkoxy group Chemical group 0.000 description 6
- 239000000460 chlorine Substances 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 150000001408 amides Chemical class 0.000 description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 5
- 229910052736 halogen Inorganic materials 0.000 description 5
- 150000002367 halogens Chemical group 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 229910000027 potassium carbonate Inorganic materials 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- QUEAUAPFDVCMFQ-UHFFFAOYSA-N 2-[(3-phenyl-1,2,4-thiadiazol-5-yl)sulfanyl]acetic acid Chemical compound S1C(SCC(=O)O)=NC(C=2C=CC=CC=2)=N1 QUEAUAPFDVCMFQ-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 239000004480 active ingredient Substances 0.000 description 4
- 229910052783 alkali metal Inorganic materials 0.000 description 4
- 125000000304 alkynyl group Chemical group 0.000 description 4
- 239000004009 herbicide Substances 0.000 description 4
- 230000001069 nematicidal effect Effects 0.000 description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 159000000000 sodium salts Chemical class 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 241000244206 Nematoda Species 0.000 description 3
- 125000003342 alkenyl group Chemical group 0.000 description 3
- 125000005907 alkyl ester group Chemical group 0.000 description 3
- SFZULDYEOVSIKM-UHFFFAOYSA-N chembl321317 Chemical compound C1=CC(C(=N)NO)=CC=C1C1=CC=C(C=2C=CC(=CC=2)C(=N)NO)O1 SFZULDYEOVSIKM-UHFFFAOYSA-N 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 230000009036 growth inhibition Effects 0.000 description 3
- 230000002363 herbicidal effect Effects 0.000 description 3
- 239000003701 inert diluent Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 230000000638 stimulation Effects 0.000 description 3
- 125000000547 substituted alkyl group Chemical group 0.000 description 3
- LDKHLTLTGGUBOG-UHFFFAOYSA-N 3-methyl-5-methylsulfanyl-1,2,4-thiadiazole Chemical compound CSC1=NC(C)=NS1 LDKHLTLTGGUBOG-UHFFFAOYSA-N 0.000 description 2
- NAKQCFRTJSBUPT-UHFFFAOYSA-N 3-phenyl-2h-1,2,4-thiadiazole-5-thione Chemical compound S1C(S)=NC(C=2C=CC=CC=2)=N1 NAKQCFRTJSBUPT-UHFFFAOYSA-N 0.000 description 2
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- 240000006240 Linum usitatissimum Species 0.000 description 2
- 235000004431 Linum usitatissimum Nutrition 0.000 description 2
- 241000209082 Lolium Species 0.000 description 2
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 2
- 244000141359 Malus pumila Species 0.000 description 2
- 235000011430 Malus pumila Nutrition 0.000 description 2
- 235000015103 Malus silvestris Nutrition 0.000 description 2
- SUZRRICLUFMAQD-UHFFFAOYSA-N N-Methyltaurine Chemical compound CNCCS(O)(=O)=O SUZRRICLUFMAQD-UHFFFAOYSA-N 0.000 description 2
- 240000003768 Solanum lycopersicum Species 0.000 description 2
- 240000008042 Zea mays Species 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 239000003139 biocide Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 2
- 229940106681 chloroacetic acid Drugs 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- 239000000428 dust Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 2
- 235000004426 flaxseed Nutrition 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 150000002825 nitriles Chemical group 0.000 description 2
- 125000006501 nitrophenyl group Chemical group 0.000 description 2
- 239000003415 peat Substances 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 230000001105 regulatory effect Effects 0.000 description 2
- 230000008653 root damage Effects 0.000 description 2
- 239000004576 sand Substances 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 125000003107 substituted aryl group Chemical group 0.000 description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
- 239000004563 wettable powder Substances 0.000 description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- NRCBBTGEODPSEJ-UHFFFAOYSA-N 1,2,4-thiadiazole 1-oxide Chemical compound O=S1C=NC=N1 NRCBBTGEODPSEJ-UHFFFAOYSA-N 0.000 description 1
- VEUMBMHMMCOFAG-UHFFFAOYSA-N 2,3-dihydrooxadiazole Chemical compound N1NC=CO1 VEUMBMHMMCOFAG-UHFFFAOYSA-N 0.000 description 1
- OVSKIKFHRZPJSS-DOMIDYPGSA-N 2-(2,4-dichlorophenoxy)acetic acid Chemical compound OC(=O)[14CH2]OC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-DOMIDYPGSA-N 0.000 description 1
- OWWQHLYCQQNFTR-UHFFFAOYSA-N 2-[(3-ethyl-1,2,4-thiadiazol-5-yl)sulfanyl]acetic acid Chemical compound CCC1=NSC(SCC(O)=O)=N1 OWWQHLYCQQNFTR-UHFFFAOYSA-N 0.000 description 1
- HRSHKJAXWRORDL-UHFFFAOYSA-N 2-[(3-methyl-1,2,4-thiadiazol-5-yl)sulfanyl]acetic acid Chemical compound CC1=NSC(SCC(O)=O)=N1 HRSHKJAXWRORDL-UHFFFAOYSA-N 0.000 description 1
- DHQKINMFWJSHMT-UHFFFAOYSA-N 2-[(3-phenyl-1,2,4-oxadiazol-5-yl)sulfanyl]acetamide Chemical compound O1C(SCC(=O)N)=NC(C=2C=CC=CC=2)=N1 DHQKINMFWJSHMT-UHFFFAOYSA-N 0.000 description 1
- QPJHQHCCTYMFPQ-UHFFFAOYSA-N 2-[(3-phenyl-1,2,4-thiadiazol-5-yl)sulfanyl]acetamide Chemical compound S1C(SCC(=O)N)=NC(C=2C=CC=CC=2)=N1 QPJHQHCCTYMFPQ-UHFFFAOYSA-N 0.000 description 1
- BNYIYFFYEWFZBY-UHFFFAOYSA-N 2-[(3-phenyl-1,2,4-thiadiazol-5-yl)sulfanyl]acetonitrile Chemical compound S1C(SCC#N)=NC(C=2C=CC=CC=2)=N1 BNYIYFFYEWFZBY-UHFFFAOYSA-N 0.000 description 1
- KYNFGMNRXZPABQ-UHFFFAOYSA-N 2-[[3-(4-chlorophenyl)-1,2,4-oxadiazol-5-yl]sulfanyl]acetic acid Chemical compound O1C(SCC(=O)O)=NC(C=2C=CC(Cl)=CC=2)=N1 KYNFGMNRXZPABQ-UHFFFAOYSA-N 0.000 description 1
- WRDCUQIIJMRCFI-UHFFFAOYSA-N 2-[[3-(4-chlorophenyl)-1,2,4-thiadiazol-5-yl]sulfanyl]acetic acid Chemical compound S1C(SCC(=O)O)=NC(C=2C=CC(Cl)=CC=2)=N1 WRDCUQIIJMRCFI-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- PCJFEVUKVKQSSL-UHFFFAOYSA-N 2h-1,2,4-oxadiazol-5-one Chemical compound O=C1N=CNO1 PCJFEVUKVKQSSL-UHFFFAOYSA-N 0.000 description 1
- YGNLSZIEDZSDMJ-UHFFFAOYSA-N 3-(4-chlorophenyl)-2h-1,2,4-oxadiazole-5-thione Chemical compound O1C(S)=NC(C=2C=CC(Cl)=CC=2)=N1 YGNLSZIEDZSDMJ-UHFFFAOYSA-N 0.000 description 1
- YXKCRAHFCOHCCU-UHFFFAOYSA-N 3-(4-chlorophenyl)-5-methylsulfanyl-1,2,4-oxadiazole Chemical compound ClC1=CC=C(C=C1)C1=NOC(=N1)SC YXKCRAHFCOHCCU-UHFFFAOYSA-N 0.000 description 1
- LPXGTFJQONCRKV-UHFFFAOYSA-N 3-(4-chlorophenyl)-5-methylsulfanyl-1,2,4-thiadiazole Chemical compound S1C(SC)=NC(C=2C=CC(Cl)=CC=2)=N1 LPXGTFJQONCRKV-UHFFFAOYSA-N 0.000 description 1
- SJPHIDMWIXLEJI-UHFFFAOYSA-N 3-(4-methoxyphenyl)-5-methylsulfanyl-1,2,4-thiadiazole Chemical compound C1=CC(OC)=CC=C1C1=NSC(SC)=N1 SJPHIDMWIXLEJI-UHFFFAOYSA-N 0.000 description 1
- ICEJTCKJXMPXBW-UHFFFAOYSA-N 3-(4-methoxyphenyl)-5-prop-2-ynylsulfanyl-1,2,4-oxadiazole Chemical compound COC1=CC=C(C=C1)C1=NOC(=N1)SCC#C ICEJTCKJXMPXBW-UHFFFAOYSA-N 0.000 description 1
- UAYMEXFNQJUHAC-UHFFFAOYSA-N 3-(4-methylphenyl)-5-prop-2-ynylsulfanyl-1,2,4-oxadiazole Chemical compound C(C#C)SC1=NC(=NO1)C1=CC=C(C=C1)C UAYMEXFNQJUHAC-UHFFFAOYSA-N 0.000 description 1
- FHMDSPSKFNNEFB-UHFFFAOYSA-N 3-(4-methylphenyl)-5-prop-2-ynylsulfanyl-1,2,4-thiadiazole Chemical compound C1=CC(C)=CC=C1C1=NSC(SCC#C)=N1 FHMDSPSKFNNEFB-UHFFFAOYSA-N 0.000 description 1
- CAJLLDMXFPPSMQ-UHFFFAOYSA-N 3-[(3-phenyl-1,2,4-thiadiazol-5-yl)sulfanyl]propanoic acid Chemical compound S1C(SCCC(=O)O)=NC(C=2C=CC=CC=2)=N1 CAJLLDMXFPPSMQ-UHFFFAOYSA-N 0.000 description 1
- OQARDMDISVUHQD-UHFFFAOYSA-N 3-ethyl-5-prop-2-ynylsulfanyl-1,2,4-thiadiazole Chemical compound CCC1=NSC(SCC#C)=N1 OQARDMDISVUHQD-UHFFFAOYSA-N 0.000 description 1
- QPHZWABVAIGWHI-UHFFFAOYSA-N 3-methyl-2h-1,2,4-thiadiazole-5-thione Chemical compound CC1=NSC(S)=N1 QPHZWABVAIGWHI-UHFFFAOYSA-N 0.000 description 1
- DTVFOCDZHQJZMW-UHFFFAOYSA-N 3-methyl-5-prop-2-ynylsulfanyl-1,2,4-thiadiazole Chemical compound CC1=NSC(SCC#C)=N1 DTVFOCDZHQJZMW-UHFFFAOYSA-N 0.000 description 1
- KLUJJBZDBBYZEJ-UHFFFAOYSA-N 3-phenyl-2h-1,2,4-oxadiazole-5-thione Chemical compound N1OC(=S)N=C1C1=CC=CC=C1 KLUJJBZDBBYZEJ-UHFFFAOYSA-N 0.000 description 1
- YPNMWTNXAWZPTH-UHFFFAOYSA-N 3-phenyl-5-prop-2-ynylsulfanyl-1,2,4-oxadiazole Chemical compound O1C(SCC#C)=NC(C=2C=CC=CC=2)=N1 YPNMWTNXAWZPTH-UHFFFAOYSA-N 0.000 description 1
- IGDTTWMGHNKINM-UHFFFAOYSA-N 3-phenyl-5-prop-2-ynylsulfanyl-1,2,4-thiadiazole Chemical compound S1C(SCC#C)=NC(C=2C=CC=CC=2)=N1 IGDTTWMGHNKINM-UHFFFAOYSA-N 0.000 description 1
- NXUKPGBGOCNCCF-UHFFFAOYSA-N 5-decylsulfanyl-3-methyl-1,2,4-thiadiazole Chemical compound CCCCCCCCCCSC1=NC(C)=NS1 NXUKPGBGOCNCCF-UHFFFAOYSA-N 0.000 description 1
- LRDUJHPJSNSGDT-UHFFFAOYSA-N 5-methylsulfanyl-3-phenyl-1,2,4-oxadiazole Chemical compound O1C(SC)=NC(C=2C=CC=CC=2)=N1 LRDUJHPJSNSGDT-UHFFFAOYSA-N 0.000 description 1
- BCKNSBBDDVYPER-UHFFFAOYSA-N 5-methylsulfanyl-3-phenyl-1,2,4-thiadiazole Chemical compound S1C(SC)=NC(C=2C=CC=CC=2)=N1 BCKNSBBDDVYPER-UHFFFAOYSA-N 0.000 description 1
- JKQANWIOGLDFNT-UHFFFAOYSA-N 5-methylsulfanyl-3-propyl-1,2,4-thiadiazole Chemical compound CCCC1=NSC(SC)=N1 JKQANWIOGLDFNT-UHFFFAOYSA-N 0.000 description 1
- KXDZRJBWIXNFCH-UHFFFAOYSA-N 5-octylsulfanyl-3-phenyl-1,2,4-thiadiazole Chemical compound S1C(SCCCCCCCC)=NC(C=2C=CC=CC=2)=N1 KXDZRJBWIXNFCH-UHFFFAOYSA-N 0.000 description 1
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- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
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- LZZYPRNAOMGNLH-UHFFFAOYSA-M Cetrimonium bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+](C)(C)C LZZYPRNAOMGNLH-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
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- 150000007513 acids Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
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- 239000004411 aluminium Substances 0.000 description 1
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- 150000001412 amines Chemical class 0.000 description 1
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- 239000007864 aqueous solution Substances 0.000 description 1
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- JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- MXOQNVMDKHLYCZ-UHFFFAOYSA-N benzamidoxime Chemical compound ON=C(N)C1=CC=CC=C1 MXOQNVMDKHLYCZ-UHFFFAOYSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- QKSKPIVNLNLAAV-UHFFFAOYSA-N bis(2-chloroethyl) sulfide Chemical compound ClCCSCCCl QKSKPIVNLNLAAV-UHFFFAOYSA-N 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- JIJAYWGYIDJVJI-UHFFFAOYSA-N butyl naphthalene-1-sulfonate Chemical class C1=CC=C2C(S(=O)(=O)OCCCC)=CC=CC2=C1 JIJAYWGYIDJVJI-UHFFFAOYSA-N 0.000 description 1
- 235000013877 carbamide Nutrition 0.000 description 1
- CVXBEEMKQHEXEN-UHFFFAOYSA-N carbaryl Chemical compound C1=CC=C2C(OC(=O)NC)=CC=CC2=C1 CVXBEEMKQHEXEN-UHFFFAOYSA-N 0.000 description 1
- 229960005286 carbaryl Drugs 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
- 239000002361 compost Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 150000001880 copper compounds Chemical class 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000006003 dichloroethyl group Chemical group 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- MCWXGJITAZMZEV-UHFFFAOYSA-N dimethoate Chemical compound CNC(=O)CSP(=S)(OC)OC MCWXGJITAZMZEV-UHFFFAOYSA-N 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- KWABLUYIOFEZOY-UHFFFAOYSA-N dioctyl butanedioate Chemical compound CCCCCCCCOC(=O)CCC(=O)OCCCCCCCC KWABLUYIOFEZOY-UHFFFAOYSA-N 0.000 description 1
- 239000012990 dithiocarbamate Substances 0.000 description 1
- 150000004659 dithiocarbamates Chemical class 0.000 description 1
- 235000005489 dwarf bean Nutrition 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- VTBNGZKREZTGKE-UHFFFAOYSA-N ethyl 2-[(3-phenyl-1,2,4-oxadiazol-5-yl)sulfanyl]acetate Chemical compound O1C(SCC(=O)OCC)=NC(C=2C=CC=CC=2)=N1 VTBNGZKREZTGKE-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- UAYKGOMDUQLCJS-UHFFFAOYSA-N ethylsulfanyl acetate Chemical compound CCSOC(C)=O UAYKGOMDUQLCJS-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 150000002194 fatty esters Chemical class 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 125000001475 halogen functional group Chemical group 0.000 description 1
- 125000005059 halophenyl group Chemical group 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 239000006028 limestone Substances 0.000 description 1
- 235000009973 maize Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- 235000010460 mustard Nutrition 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 125000001477 organic nitrogen group Chemical group 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 238000004382 potting Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- YORCIIVHUBAYBQ-UHFFFAOYSA-N propargyl bromide Chemical compound BrCC#C YORCIIVHUBAYBQ-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000013585 weight reducing agent Substances 0.000 description 1
- 239000012991 xanthate Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
- C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D271/06—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles
- C07D271/07—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/08—1,2,4-Thiadiazoles; Hydrogenated 1,2,4-thiadiazoles
Definitions
- the present invention is also for a process for the treatment of plants, the soil, land or aquatic areas, for the control of unwanted plants or pests, or for the modification of plants, which comprises applying thereon or thereto a diazole of Formula I or a composition containing the same.
- the diazoles of Formula I may be prepared by the treatment of the corresponding S-mercapto substituted diazole of Formula II,
- Inert diluents with which the diazoles may be incorporated include solid inert media comprising powdered or divided solid materials, for example, clays, sands, talc, mica, peat, fertilizers and soil, such products either comprising dust or larger particle size materials. If desired the diazoles of Formula I may be used to impregnate or coat preformed granules such as limestone or peat granules.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB5124869 | 1969-10-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3770754A true US3770754A (en) | 1973-11-06 |
Family
ID=10459243
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US00080165A Expired - Lifetime US3770754A (en) | 1969-10-18 | 1970-10-12 | Certai 1,2,4-oxa- and -thiadiazol-5-ylthioalkanoic acid derivatives |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US3770754A (nl) |
| JP (1) | JPS5510564B1 (nl) |
| BE (1) | BE757577A (nl) |
| CA (1) | CA935818A (nl) |
| DE (1) | DE2050346A1 (nl) |
| ES (1) | ES384420A1 (nl) |
| FR (1) | FR2066057A5 (nl) |
| GB (1) | GB1328964A (nl) |
| IE (1) | IE34568B1 (nl) |
| IL (1) | IL35405A (nl) |
| NL (1) | NL167427C (nl) |
| SE (1) | SE394072B (nl) |
| ZA (1) | ZA706750B (nl) |
Cited By (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4092149A (en) * | 1976-05-15 | 1978-05-30 | Fisons Limited | Method of increasing the yield of cotton plants |
| US4141716A (en) * | 1975-02-12 | 1979-02-27 | Fisons Limited | Method for increasing yield of soy beans |
| US4279638A (en) * | 1979-08-13 | 1981-07-21 | Stauffer Chemical Company | 3,5-Disubstituted 1,2,4-oxadiazole herbicidal antidotes |
| US4578477A (en) * | 1979-12-31 | 1986-03-25 | Monsanto Company | N-substituted benzothiazoline and N-substituted benzoxazoline derivatives |
| EP0217747A2 (de) * | 1985-09-30 | 1987-04-08 | Ciba-Geigy Ag | Nematizide Mittel |
| EP0285565A2 (de) * | 1987-04-03 | 1988-10-05 | Ciba-Geigy Ag | 2-Mercapto-5-pyridyl-1,3,4-oxadiazole und -1,3,4-thiadiazole, Verfahren zu ihrer Herstellung und ihre Verwendung als nematizide Mittel |
| US4861367A (en) * | 1987-04-03 | 1989-08-29 | Ciba-Geigy Corporation | 2-Mercapto-5-pyrazinyl-1,3,4-oxadiazoles or 2-mercapto-5-pyrazinyl-1,3,4-thiadiazoles as nematicides |
| US4910210A (en) * | 1987-12-18 | 1990-03-20 | Ciba-Geigy Corp. | Nematicidal compositions |
| EP0389426A1 (de) * | 1989-03-21 | 1990-09-26 | Ciba-Geigy Ag | Nematizide und fungizide Mittel |
| US5013745A (en) * | 1988-09-23 | 1991-05-07 | Ciba-Geigy Corporation | Nematicidal compositions |
| US5162349A (en) * | 1988-09-23 | 1992-11-10 | Ciba-Geigy Corporation | Nematocidal and fungicidal compositions |
| US9420788B2 (en) | 2007-08-13 | 2016-08-23 | Monsanto Technology Llc | Compositions and methods for controlling nematodes |
| US9426995B2 (en) | 2009-02-10 | 2016-08-30 | Monsanto Technology Llc | Compositions and methods for controlling nematodes |
| US9961899B2 (en) | 2012-12-04 | 2018-05-08 | Monsanto Technology Llc | Nematicidal aqueous suspension concentrate compositions |
| US11905262B1 (en) | 2023-10-11 | 2024-02-20 | King Faisal University | N′-(2-(5-(4-chlorophenyl)-1,3,4-oxadiazol-2-ylthio)acetoxy)-2-naphthimidamide as an antimicrobial compound |
| US11926621B1 (en) | 2023-10-12 | 2024-03-12 | King Faisal University | N′-(2-(5-(4-chlorophenyl)-1,3,4-oxadiazol-2-ylthio)acetoxy)benzo[d][1,3]dioxole-5-carboximidamide as an antimicrobial compound |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| USRE29439E (en) * | 1969-10-18 | 1977-10-11 | Fisons Limited | Certain 1,2,4-Oxa- and -thiadiazol-5-ylthioalkanoic acid derivatives |
| DE2946524A1 (de) * | 1979-11-17 | 1981-06-11 | Bayer Ag, 5090 Leverkusen | Azolyloxy-carbonsaeure-n-oxy-amide, verfahren zu ihrer herstellung und ihre verwendung als herbizide |
| EP0263066A3 (de) * | 1986-09-26 | 1988-06-01 | Ciba-Geigy Ag | 2-Mercapto-oxadiazol- und -thiadiazol-Derivate, Verfahren zu ihrer Herstellung und diese enthaltende nematizide Mittel |
| GB8801289D0 (en) * | 1988-01-21 | 1988-02-17 | Shell Int Research | Oxadiazole compounds their preparation & their use as pesticides |
| DE3910358A1 (de) | 1989-03-31 | 1990-10-04 | Bayer Ag | Thiadiazol-substituierte acrylsaeureester und neue zwischenprodukte |
| DE4131138A1 (de) * | 1991-09-19 | 1993-03-25 | Bayer Ag | 3-(4-bromphenyl)-5-methylsulfonyl-1,2,4- thiadiazol,ein verfahren zur herstellung, seine verwendung und neue zwischenprodukte |
| US20220280487A1 (en) * | 2019-08-26 | 2022-09-08 | Stichting Vumc | Inhibition of mycobacterial type vii secretion |
-
0
- BE BE757577D patent/BE757577A/xx unknown
-
1969
- 1969-10-18 GB GB5124869A patent/GB1328964A/en not_active Expired
-
1970
- 1970-10-05 ZA ZA706750A patent/ZA706750B/xx unknown
- 1970-10-07 IL IL35405A patent/IL35405A/xx unknown
- 1970-10-09 IE IE1298/70A patent/IE34568B1/xx unknown
- 1970-10-10 ES ES384420A patent/ES384420A1/es not_active Expired
- 1970-10-12 US US00080165A patent/US3770754A/en not_active Expired - Lifetime
- 1970-10-13 CA CA095318A patent/CA935818A/en not_active Expired
- 1970-10-13 NL NL7014971.A patent/NL167427C/nl not_active IP Right Cessation
- 1970-10-14 DE DE19702050346 patent/DE2050346A1/de not_active Ceased
- 1970-10-16 FR FR7037379A patent/FR2066057A5/fr not_active Expired
- 1970-10-16 SE SE7014027A patent/SE394072B/xx unknown
- 1970-10-17 JP JP9093770A patent/JPS5510564B1/ja active Pending
Cited By (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4141716A (en) * | 1975-02-12 | 1979-02-27 | Fisons Limited | Method for increasing yield of soy beans |
| US4092149A (en) * | 1976-05-15 | 1978-05-30 | Fisons Limited | Method of increasing the yield of cotton plants |
| US4279638A (en) * | 1979-08-13 | 1981-07-21 | Stauffer Chemical Company | 3,5-Disubstituted 1,2,4-oxadiazole herbicidal antidotes |
| US4578477A (en) * | 1979-12-31 | 1986-03-25 | Monsanto Company | N-substituted benzothiazoline and N-substituted benzoxazoline derivatives |
| EP0217747B1 (de) * | 1985-09-30 | 1991-11-21 | Ciba-Geigy Ag | Nematizide Mittel |
| EP0217747A2 (de) * | 1985-09-30 | 1987-04-08 | Ciba-Geigy Ag | Nematizide Mittel |
| EP0285565A2 (de) * | 1987-04-03 | 1988-10-05 | Ciba-Geigy Ag | 2-Mercapto-5-pyridyl-1,3,4-oxadiazole und -1,3,4-thiadiazole, Verfahren zu ihrer Herstellung und ihre Verwendung als nematizide Mittel |
| EP0285565A3 (en) * | 1987-04-03 | 1989-03-15 | Ciba-Geigy Ag | 2-mercapto-5-pyridyl-1,3,4-oxadiazoles and 1,3,4-thiadiazoles, process for their preparation and their use as nematicidal agents |
| US4861367A (en) * | 1987-04-03 | 1989-08-29 | Ciba-Geigy Corporation | 2-Mercapto-5-pyrazinyl-1,3,4-oxadiazoles or 2-mercapto-5-pyrazinyl-1,3,4-thiadiazoles as nematicides |
| US4910210A (en) * | 1987-12-18 | 1990-03-20 | Ciba-Geigy Corp. | Nematicidal compositions |
| US5162349A (en) * | 1988-09-23 | 1992-11-10 | Ciba-Geigy Corporation | Nematocidal and fungicidal compositions |
| US5013745A (en) * | 1988-09-23 | 1991-05-07 | Ciba-Geigy Corporation | Nematicidal compositions |
| EP0389426A1 (de) * | 1989-03-21 | 1990-09-26 | Ciba-Geigy Ag | Nematizide und fungizide Mittel |
| US10112930B2 (en) | 2007-08-13 | 2018-10-30 | Monsanto Technology Llc | Compositions and methods for controlling nematodes |
| US9420788B2 (en) | 2007-08-13 | 2016-08-23 | Monsanto Technology Llc | Compositions and methods for controlling nematodes |
| US9642364B2 (en) | 2007-08-13 | 2017-05-09 | Monsanto Technology Llc | Compositions and methods for controlling nematodes |
| US10827753B2 (en) | 2007-08-13 | 2020-11-10 | Monsanto Technology Llc | Compositions and methods for controlling nematodes |
| US10375958B2 (en) | 2007-08-13 | 2019-08-13 | Monsanto Technology Llc | Compositions and methods for controlling nematodes |
| US9426995B2 (en) | 2009-02-10 | 2016-08-30 | Monsanto Technology Llc | Compositions and methods for controlling nematodes |
| US9820486B2 (en) | 2009-02-10 | 2017-11-21 | Monsanto Technology Llc | Compositions and methods for controlling nematodes |
| US10117434B2 (en) | 2012-12-04 | 2018-11-06 | Monsanto Technology Llc | Nematicidal aqueous suspension concentrate compositions |
| US9961899B2 (en) | 2012-12-04 | 2018-05-08 | Monsanto Technology Llc | Nematicidal aqueous suspension concentrate compositions |
| US10499645B2 (en) | 2012-12-04 | 2019-12-10 | Monsanto Technology, Llc | Nematicidal aqueous suspension concentrate compositions |
| US11905262B1 (en) | 2023-10-11 | 2024-02-20 | King Faisal University | N′-(2-(5-(4-chlorophenyl)-1,3,4-oxadiazol-2-ylthio)acetoxy)-2-naphthimidamide as an antimicrobial compound |
| US11976051B1 (en) | 2023-10-11 | 2024-05-07 | King Faisal University | N′-(2-(5-(4-chlorophenyl)-1,3,4-oxadiazol-2-ylthio)acetoxy)-2-naphthimidamide as an antimicrobial compound |
| US11926621B1 (en) | 2023-10-12 | 2024-03-12 | King Faisal University | N′-(2-(5-(4-chlorophenyl)-1,3,4-oxadiazol-2-ylthio)acetoxy)benzo[d][1,3]dioxole-5-carboximidamide as an antimicrobial compound |
Also Published As
| Publication number | Publication date |
|---|---|
| IE34568B1 (en) | 1975-06-11 |
| NL7014971A (nl) | 1971-04-20 |
| NL167427B (nl) | 1981-07-16 |
| GB1328964A (en) | 1973-09-05 |
| IE34568L (en) | 1971-04-18 |
| JPS5510564B1 (nl) | 1980-03-17 |
| IL35405A (en) | 1975-06-25 |
| CA935818A (en) | 1973-10-23 |
| IL35405A0 (en) | 1970-12-24 |
| DE2050346A1 (de) | 1971-04-29 |
| NL167427C (nl) | 1981-12-16 |
| ES384420A1 (es) | 1973-06-16 |
| ZA706750B (en) | 1971-07-28 |
| BE757577A (fr) | 1971-04-15 |
| FR2066057A5 (nl) | 1971-08-06 |
| SE394072B (sv) | 1977-06-06 |
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